When famous folk from the worlds of sports, entertainment and business want to see their versions of venerated celebrities, many of them flock to high-stakes poker tables around the world. Inclined to chase straights when they’re not closing deals or making movies, they afford themselves opportunities to see how the pros do it — and hope to win a bit of private-jet gas money in the process.
Oscar-winning actor Ben Affleck, for example, takes the game seriously enough that he actually received poker lessons from the strategically gifted former-pro Annie Duke. While Affleck is known for playing in private games where buy-ins supposedly stretch toward $100,000, he publicly proved his mettle in 2004 by winning the California State Poker Championship with a first prize of $356,400. Affleck’s last notable showing as a gambler? Getting booted from the Hard Rock for card counting, but that’s a whole other story.
Poker superstar Phil Hellmuth tells Casinomir that he’s played against Affleck and respects the actor’s game. “We teased each other and had a lot of fun,” he says, adding that James Woods is another talented celeb on the circuit. “He’s a hell of a tournament player and very intelligent.”
Hedge-fund wizard David Einhorn beat the pros at their own game when he took down $4,352,000 for finishing third in a high-roller tournament during the 2012 World Series of Poker. Tennis star Rafael Nadal has proven himself to be way better on clay than he is on felt while Olympic swimmer Michael Phelps once shared a house with poker pro Jeff Gross – and, apparently learned a thing or two. “Mike is easily one of the best celebrity poker players around,” Gross has said.
Comedian Kevin Hart is no joke at the poker table, though he has had his share of good luck. Playing in a 2018 televised poker tournament, he misread his cards, continued through a hand he shouldn’t have been in and still managed to win. His total tournament take is in the $50,000 range. Hart, currently recovering from a car accident, recently signed a sponsorship agreement with PokerStars. Soon after inking the deal, he declared, “I am going to make poker fun again. I love the game, I love to live, I love to laugh and I am going to bring this energy to the game of poker.”
The billionaire Texas banker Andy Beal played some of the richest poker in the world, when he took on a cadre of professionals — including Phil Ivey, Doyle Brunson and late, great Chip Reese — for multi-million-dollar games of heads-up Texas hold’em. Though he ultimately lost to the group that dubbed itself The Corporation, Beal logged some memorable wins. During an intense series of legendary matches at Wynn Las Vegas, in 2006, he beat them out of some $13.6 million. That one outcome was potentially disastrous for the pros, but it was hardly the norm. Overall, Beal dropped 10s of millions of dollars to the superior group. Apparently, he continues to play the game, but he goes up against considerably softer competition.
One fellow mogul unlikely to take on Beal is Carl Icahn, an entrepreneur whose holdings include more than 20 percent of Caesars Entertainment, the parent company of Caesars Palace. In considering his fellow billionaire’s poker skills, Icahn — who is an avid card shark — has said, “I always thought of myself as a good player. But I’m not in his league.”
Beal and Icahn are not alone in welcoming poker as a mental getaway from the rigors of doing business. Hellmuth frequently squares off with his buddy and venture capitalist Chamath Palihapitiya, a part-owner of the Golden State Warriors basketball team. They play together in what has come to be known as the Silicon Valley Game. Others at the table are said to include Craft Ventures co-founder Bill Lee (to whom Hellmuth gifted his 15th World Series of Poker bracelet) and angel investor Jason Calacanis. Then there are the celebrated athletes who actually come to Las Vegas in order to take on the Poker Brat. “My favorite celebrity to play against is [Los Angeles Laker] Draymond Green,” Hellmuth says. “He plays excellent poker and flies down to Aria [for games].”
Though Hellmuth might be the more seasoned hustler here, don’t feel too bad for his well-heeled opponents. Hellmuth insists that skills in business cross over to skills in poker. “In general, great businessmen are great poker players,” he told Business Insider. “There’s a reason these guys made so much money in the real world.”
# # #
ABOUT MICHAEL KAPLAN
With four books (and more on the way) plus hundreds articles, Michael Kaplan is one of the most experienced writer in gambling related subjects.
He have covered big stories including famous gamblers such as Phil Ivey and Phil Hellmuth for publications including Wired, Playboy, Cigar Aficionado, New York Post and New York Times. Based in New York, where he regularly writes for the Post.